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E4c063735c7cb01a826cc1875a25383c Zps791baf20 by Tgread

"What do you mean, you lost my luggage?"

I had landed on the island not five minutes ago, and already I was in a heated discussion with the woman at the front desk in my hotel. Well, it was heated on my end. She seemed as serene as a summer breeze.

"I am terribly sorry sir, but there is nothing we can do for you at this time. Your belongings will be given utmost search priority. In the meantime, would you like to try the Shoujo Island Premium Package? Given your circumstances, we can give it to you at a significant discount. It comes with complimentary recreational clothing and swimwear."

"..All right, fine. I just want to get to my room."

I glumly looked around the hotel lobby. It's true, this place really is a paradise. It's the highest rated vacation spot in the entire Western Hemisphere. Yet, I couldn't help but think about Amanda.

Amanda was my girlfriend for the past three years. I won this trip to Shoujo Island from work and was excited to surprise her with the tickets. She surprised me first by dumping me the night before the trip was scheduled. I was acutely aware of a small, black box in my pants pocket, leaving me a haunting reminder of my original intentions for this weekend. I thought for sure that Amanda would be the one I spent the rest of my life beside.  Yet here I stand- alone in the most romantic spot on the planet.  In fact, my only belonging that was not lost on the flight was that diamond ring, still hiding in the folds of my pocket. Oh, the irony.

"Right this way, sir. Cassidy will show you to your room."

I followed the bouncing young Cassidy over to the elevator and we went up to the fifth floor. As the door opened, my spirits lifted significantly- before me was a hall of doors, filled with bikini-clad young women, all talking and giggling one with another.  Maybe this wasn't such a bad place to be single.  As Cassidy led me down the hall to my room, three brunettes approached me. The most well endowed spoke to me.

"Hey, my name's Jessica. We couldn't help but notice you come in. We're all going to the pool in a minute. Want to join?"

"I'm not sure if I should.." I responded bashfully.

"Come on! What do you have to lose? You have a girlfriend or something?"

"Erm, well.. Not anymore, I guess." I muttered with a twinge of sadness.  The three girls all responded with an empathetic, "Awwh" and hugged him.

"Well, that's that!" Jessica perked up, "You are coming with us and we're not taking no for an answer!"

Before I could refute, Cassidy called from down the hall to tell me my room was ready. I quickly waved goodbye to the ladies and walked down to room 513. It was quite the room. King sized bed, panoramic window on the far side overlooking the beach, and plenty spacious. I wish I lived like this at home. I thought.

"You'll find everything you need is already stocked in the room, sir." Cassidy motioned to the fridge, and the bathroom amenities.  "And clothes have been provided for you in the wardrobes, as per your Premium Package dictates. Is there anything else you require?"

"No, looks real good. Thank you.. Cassidy, was it?"

She curtsied deeply and grinned at me. "At your service. Just let me know if you need anything."

Cassidy left the room, giving me a chance to really take it in.  This place was incredible. It's too bad my reservation is only for the weekend.  Running my hand against the furniture, I could feel the carefully crafted detail. The bed was extremely soft. Maybe I could take a quick nap.. I thought.

My mind was drawn back to the ladies in the hall. They invited me to go swimming. And Cassidy did say that clothes are provided...

I undressed down to my boxers and began searching through one of the closets. That's funny, I thought, This closet only has women's dresses in it.. I moved on to the next door, only to find a similar pattern- dresses, shoes, undergarments, swimwear, formal attire.. It was all women's clothing!

There must be a mistake, I thought, picking up the phone to call the front desk. This had to be sorted out. The phone began ringing and I waited. Then again.. Curiosity bubbled up inside of me. I've always kind of wanted to try this.. The phone line sprung to life with the voice of the lady at the front desk.

<< Front desk, how may we be of service? >>

I promptly hung up the phone.  A little bit of time to myself could be nice.

After making sure the front door was locked, I laid several options from the clothes in the closets. With a slight degree of difficulty, I pulled on a green satin dress. It hugged around my waist and was slightly loose around the chest, but it felt nice. Next, a bit more casual of attire- a yellow flowered blouse and red miniskirt. I looked in the mirror, turning back and forth to get a good view from all angles. This was kind of fun. I tried several more outfits-a blue sleeveless turtleneck with black pencil skirt, a pink toy shirt and skinny jeans, even what appeared to be a cheerleading uniform.  

I had just pulled on a cute blue two piece bikini, complete with miniskirt bottom, when I heard a swift knock at my door. I jolted, paralyzed by fear as the door opened to reveal Cassidy and the brunette girls from earlier.

"We got your call, but couldn't hear you, sir, so I was sent to check on-" she halted in the entryway as she noticed me, fully clad in the feminine swimwear. "Oh my."

"It's not what you think!" I started, but before I could finish, the girls all started clamoring at once.

"Where did you GET that?"

"That really accents your eyes."

"I wish I could pull that look off."

I stared, stunned.  Are they serious? Jessica grabbed my hand and started tugging at me.

"This is perfect! Just your style. Now that you're ready, you can come with us to the pool!"

"No!" I asserted, "I'll be the laughingstock of the resort!"

"Oh, come now, sir." Cassidy soothed, "Nothing of the sort will happen. You really do look quite lovely."

I would have considered it further, but before I could do anything, I was yanked out the door and down the hall. We approached the pool area, where I could see large crowds of people.

What have I gotten myself into?

To Be Continued...
Story inspired by the group "Turn Into A Girl" and it's group blog feature "TG Caption This"

This may not be conventional, but I saw a lot of promise in this picture. I'm going to release the story in parts.
Add a Comment:
Shulkielover Featured By Owner Oct 15, 2015  Student Writer
Where is the next part?
dimencio20 Featured By Owner May 15, 2014
chekm8 Featured By Owner May 14, 2014
Looks good so far!
MikotoWolfskin Featured By Owner May 13, 2014  Hobbyist Digital Artist
Taking it nice and slow, I like it, full of detail. Very nice looking forward to the next part :)
Tgread Featured By Owner May 14, 2014  Hobbyist Writer
Thanks! I will try not to disappoint!
GoodKittyNyanchan Featured By Owner May 13, 2014  Hobbyist Writer
:iconkyokokyutplz: At least he's properly dressed-nya. :giggle: :iconazu-nyanplz: 
Tgread Featured By Owner May 14, 2014  Hobbyist Writer
Oh, all too properly dressed :) Much more twists to come!
Add a Comment:

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Submitted on
May 13, 2014


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